1. My first time as a bottom and with a tranny


    Date: 9/29/2015, Categories: Anal, First Time, Shemales, Author: Pepmeister, Rating: 100, Source: xHamster

    So this is the story about how i got my first experience being a bottom, and why it was with a tranny I was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the tranny porn was the best. The idea of having a beautiful woman fuck me was very very exiting for me. So this one night, I was jerking off and then i thought to myself &#034why not?&#034. Went into the local gay chat room and started looking for someone to &#034get together with&#034. But the idea of having a man on top of me was not what I wanted, I didn't wanted to have sex with a guy, i just wanted to have sex with a cock. So the idea came to mind, Why not go for a tranny?. Went on google and searched for tranny e****ts on my area, and to my surprise the market was huge!!! beautiful shemales offering sex (of course it was not for free, but who cares?). I spent a few minutes checking and decided for this brunette, long haired, girly, big breasted and with a big dick shemale. I dialed her number on my phone, but for some reason I had a hard time pushing the &#034Dial&#034 key. Until I did. The phone rang a few times until a very sweet voice answered, she sounded sexy and friendly, we spoke ...
    for a few moment and I told her that I was looking for my first time, not only with a shemale but as bottom all together. She laughed a little, and told me to come over, that she had experience with &#034first timers&#034 I jumped into the car and drove to her place. Rang the door bell, it was an intercom of a building with no doorman, she opened the door for me and told me to go in. When I got to her apartment she was even more beautiful than the pictures. About my height (5'9&#034), big breasted, she was wearing a tight black and very short dress, showing all her curves. Invited me in and we sat on the living room for a little while, gave a glass of water and we started chatting. She asked what was my fantasy, and I answered &#034I want to be bottom... with everything that means. I want to do oral, and be bottom. I'm only afraid it may hurt a lot&#034, she chuckled and told me &#034don't worry, it won't hurt. Come on, come with me&#034 she took my hand and lead me to her room. The light was dimmed, a big bed, it was quite high, on the tv was playing a porn movie, and i saw by the night stand a big bottle of lube, condoms and a roll of toilet paper. She told me to get naked and that she will be right back, and left the room. I undressed, all but my boxers. When she came back she was no longer wearing the dress, she had on a lingerie set... she looked stunning. We started kissing, very wet and passionate kisses. I started touching her boobs and butt and she also was touching ...
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